Thienopyridone derivatives as kinase inhibitors

1. A compound of formula (1):

wherein:

Y is a linking group —C(O)— or —S(O) 2 —;

n is zero or the integer 1;

m is the integer 1, 2, 3 or 4;

p is the integer 1, 2, 3 or 4;

R d is —OH, -(Alk 2 )OH, —OR 1 , -(Alk 2 )OR 1 , —NR 2 R 3 , -(Alk 2 )NR 2 R 3 or a straight or branched C 1-6 alkyl group;

Alk 2 is a straight or branched C 1-4 alkylene chain;

R 1 is a straight or branched C 1-6 alkyl group;

R 2 and R 3 , which may be the same or different, are each independently a hydrogen atom or a straight or branched C 1-6 alkyl group;

Alk 1 is a straight or branched C 1-4 alkylene chain;

Cy 1 is an optionally substituted cycloaliphatic, aromatic or heteroaromatic group; and

Ar is an optionally substituted aromatic or heteroaromatic group; or a salt or N-oxide thereof.

2. A compound as claimed in claim 1 wherein R d is —OH, -(Alk 2 )OH, -(Alk 2 )OR 1 , —NR 2 R 3 or -(Alk 2 )NR 2 R 3 .

3. A compound as claimed in claim 1 wherein Alk 2 is —CH 2 — or —C(CH 3 ) 2 —.

4. A compound as claimed in claim 1 wherein R 1 is methyl.

5. A compound as claimed in claim 1 wherein R 2 is hydrogen or methyl.

6. A compound as claimed in claim 1 wherein R 3 is hydrogen or methyl.

7. A compound as claimed in claim 1 wherein Cy 1 is phenyl, fluorophenyl, chlorophenyl, methylphenyl or cyclopropyl.

8. A compound as claimed in claim 1 wherein Ar is phenyl, difluorophenyl, (chloro)(fluoro)phenyl, (fluoro)(methyl)phenyl, chlorophenyl, cyanophenyl or methylphenyl.

9. A compound as claimed in claim 1 that is

3-[(2,4-Difluorophenyl)amino]-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(2R)-2-(Hydroxymethyl)pyrrolidin-1-yl]carbonyl}-3-[(3-methylphenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(3-Chlorophenyl)amino]-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-(4-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(2R)-2-(hydroxymethyl)-pyrrolidin-1-yl]carbonyl}-7-(4-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

2-{[(2R)-2-(Hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-(4-methylphenyl)-3-[(3-methylphenyl)amino]thieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-7-(4-fluorophenyl)-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-7-(4-fluorophenyl)-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

7-(2-Chlorophenyl)-3-[(4-fluoro-3-methylphenyl)amino]-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

7-(2-Chlorophenyl)-3-[(2,4-difluorophenyl)amino]-2{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

3-[(2-Chlorophenyl)amino]-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2-Chlorophenyl)amino]-2-{[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-Anilino-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-Anilino-2-{[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3[(2,4-Difluorophenyl)amino]-2-{[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-Anilino-2-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-Anilino-2-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

7-(4-Chlorophenyl)-3-[(4-fluoro-3-methylphenyl)amino]-2{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]carbonyl}-7-(3-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

2-{[(2R)-2-(Hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-(3-methylphenyl)-3-[(3-methylphenyl)amino]thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(2R)-2-(hydroxymethyl)-pyrrolidin-1-yl]carbonyl}-7-(3-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

3-[(3-Chloro-4-fluorophenyl)amino]-2-{[(2R)-2-(hydroxymethyl)-pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(3-Chloro-4-fluorophenyl)amino]-2-{[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(2R)-2-(hydroxymethyl)-pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3S,4S)-3,4-dihydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-[(3-hydroxyazetidin-1-yl)carbonyl]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(2S)-2-(1-hydroxy-1-methylethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(2R)-2-(1-hydroxy-1-methylethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2-Cyanophenyl)amino]-2-{[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2-Cyanophenyl)amino]-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-Anilino-7-(cyclopropylmethyl)-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

3-[(3-Cyanophenyl)amino]-2-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[2R)-2-(hydroxymethyl)pyrrolidin-1-yl]sulfonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(3R)-3-Aminopyrrolidin-1-yl]carbonyl}-3-[(2,4-difluorophenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(2S)-2-(Aminomethyl)pyrrolidin-1-yl]carbonyl}-3-[(2,4-difluorophenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(2R)-2-(Aminomethyl)pyrrolidin-1-yl]carbonyl}-3-[(2,4-difluorophenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3R)-3-(dimethylamino)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-[(4-hydroxypiperidin-1-yl)carbonyl]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

rac-3-[(2,4-Difluorophenyl)amino]-2-[(3-hydroxypiperidin-1-yl)carbonyl]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(3R)-3-Aminopyrrolidin-1-yl]carbonyl}-3-[(4-fluoro-3-methylphenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(2S)-2-(Aminomethyl)pyrrolidin-1-yl]carbonyl}-3-[(4-fluoro-3-methylphenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(3R)-3-(dimethylamino)-pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3R*,4S*)-3,4-dihydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2-Cyanophenyl)amino]-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2-Cyanophenyl)amino]-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

rac-2-{[3-Aminopyrrolidin-1-yl]carbonyl}-3-[(2,4-difluorophenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(3S)-3-Aminopyrrolidin-1-yl]carbonyl}-3-[(2,4-difluorophenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(3S)-3-Aminopyrrolidin-1-yl]carbonyl}-3-[(4-fluoro-3-methylphenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-7-(4-fluorophenyl)-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-7-(4-fluorophenyl)-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-7-(4-fluorophenyl)-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

7-(2-Chlorophenyl)-3[(4-fluoro-3-methylphenyl)amino]-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

7-(2-Chlorophenyl)-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}-3-[(3-methylphenyl)amino]thieno[2,3-b]pyridin-6(7H)-one;

7-(2-Chlorophenyl)-3-[(2,4-difluorophenyl)amino]-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-(4-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(3S)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-(4-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-(4-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}-7-(4-methylphenyl)thieno[2,3-b]pyridin-6(7H)-one;

3-[(4-Fluoro-3-methylphenyl)amino]-2-[(3-hydroxyazetidin-1-yl)carbonyl]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-[(4-Aminopiperidin-1-yl)carbonyl]-3-[(2,4-difluorophenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-[(3-Aminoazetidin-1-yl)carbonyl]-3-[(2,4-difluorophenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[4-(dimethylamino)piperidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[3-(dimethylamino)azetidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

3-[(2,4-Difluorophenyl)amino]-2-{[(3S)-3-(dimethylamino)pyrrolidin-1-yl]carbonyl}-7-phenylthieno[2,3-b]pyridin-6(7H)-one;

2-{[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]carbonyl}-3-[(4-fluoro-3-methylphenyl)amino]-7-phenylthieno[2,3-b]pyridin-6(7H)-one; or

7-(2-Chlorophenyl)-3-[(2,4-difluorophenyl)amino]-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[2,3-b]pyridin-6(7H)-one.

10. A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, in association with a pharmaceutically acceptable carrier.

11. A method for inhibiting p38α MAP kinase, which comprises administering to a patient in need thereof a compound of claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof.